701262-40-0

Upstream product

• 50638-08-9 5-bromo-3-methyl-1-benzofuran-2-carboxylic acid 
• 108-95-2 phenol 
• 1644570-70-6 ethyl N-4-bromophenoxyacetimidate 
• 70-70-2 4-hydroxypropiophenone 
• 146275-80-1 C₁₇H₁₅BrO₄ 
• 1542581-58-7 2-(5-bromo-2-methoxyphenyl)-1-(4-methoxyphenyl)propan-1-one 
• 1292981-77-1 2-(5-bromo-2-methoxyphenyl)-1-(4-methoxyphenyl)ethanone 
• 65440-82-6 O-(4-bromophenyl)hydroxylamine 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 41744-26-7 eupomatenoid 6 
• 163462-39-3 eupomatenoid-6 

Relevant academic research and scientific papers

Acid-mediated intermolecular C-F/C-H cross-coupling of 2-fluorobenzofurans with arenes: Synthesis of 2-arylbenzofurans

Transition-metal-free acid-promoted biaryl construction was achieved via intermolecular C-F/C-H cross-coupling. By treating 2-fluorobenzofurans with arenes in the presence of AlCl3, 2-arylbenzofurans were obtained. This protocol was successfully applied to the short-step orthogonal synthesis of a bioactive 2-arylbenzofuran natural product, which allows independent transformations of C-F and C-Br bonds. Mechanistic studies indicated that α-fluorine-stabilized carbocations, generated via the protonation of 2-fluorobenzofurans, served as key intermediates. The Friedel-Crafts-type C-C bond formation between the α-fluorocarbocations and arenes, followed by hydrogen fluoride elimination, afforded 2-arylbenzofurans. This journal is

Synthesis of Functionalized 2-(4-Hydroxyphenyl)-3-methylbenzofuran Allosteric Modulators of Hsp90 Activity

Hsp90 is a molecular chaperone that plays a pivotal role in the cell life cycle. ATP-regulated internal dynamics are critical to Hsp90 function and we recently demonstrated that these dynamics can be modulated in an allosteric fashion; the protein C-terminal domain (CTD) can be effectively targeted with a family of 2-phenyl-benzofuran derivatives. Here we describe the expansion of the initial library, reporting 28 new derivatives that explore the chemical space at opposite ends of the benzofuran scaffold. Interactions of the compounds with a full-length protein homolog were explored by Saturation Transfer Difference (STD) NMR spectroscopy. In this context we also report the interaction epitope of Novobiocin, a known CTD inhibitor.

Synthetic method for eupomatenoid-6

The present invention relates to a simple method for synthesizing a natural benzofuran derivative eupomatenoid 6 by using a horner-emmons type condensation reaction as a main step. In addition, the polarity reversal properties of an aldehyde derivative andalpha;-aminophosphonate are effectively used for the reaction. Deoxybenzoin is obtained by reacting the andalpha;-aminophosphonate from anisaldehyde with 5-bromo-2-methoxybenzaldehyde, using the horner-emmons type condensation, and then the obtained deoxybenzoin is methylated and becomes a benzofuran structure with remarkable yield via random demethylation-cyclodehydration. Finally, the eupomatenoid 6 is obtained at 56.8% of the total yield from a total of five steps by a Suzuki coupling reaction with propenyl boronic acid.COPYRIGHT KIPO 2016

Metal-free one-pot synthesis of benzofurans

Ethyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition-metal-free conditions. The obtained O-arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[b]furans through oxime formation, [3,3]-rearrangement, and cyclization in a fast and operationally simple one-pot fashion without using excess reagents. Alternatively, the O-arylated products could be isolated or transformed in situ to aryloxyamines or O-arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)-machaeriol B. Just add salt! A metal-free, room temperature arylation of ethyl acetohydroxamate, followed by an in situ reaction with ketones under acidic conditions yielded substituted benzo[b]furans in a fast and operationally simple one-pot fashion without using excess reagents (see scheme). Alternatively, the O-arylated products could be isolated, hydrolyzed in situ to aryloxyamines, or transformed to O-arylaldoximes. The efficiency of the methodology was demonstrated by the formal synthesis of several biologically active benzofurans.

An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides

An efficient and practical method for construction of 2-arylbenzo[b]furans from 2-methoxychalcone epoxides has been reported. Catalyzed by 2 mol % of BF3·Et2O, 2-methoxychalcone epoxides went through the Meerwein rearrangement, followed by deformylation in one-pot to successfully afforded 2-methoxydeoxybenzoins. Afterward, 2-arylbenzo[b]furans were obtained in high yields (87%-100%) via intermolecular cyclodehydration of 2-methoxydeoxybenzoins with 48% HBr. By utilization of this approach, the natural product stemofuran A and the key intermediate of eupomatenoid 6 have been synthesized conveniently.

Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: Short synthesis of natural 2-arylbenzofurans

A new synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic or acyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP system is found to be the most effective for constructing various benzofurans. Synthetic utility of this reaction is demonstrated by the short synthesis of natural benzofurans without protection of the hydroxy group. The synthesis of Stemofuran A was accomplished via condensation of ketones with aryloxyamine and subsequent reaction with TFAT-DMAP in a four-step synthesis with 72% overall yield. Similarly, Eupomatenoid 6 and Coumestan were synthesized through the reaction of oxime ether with TFAT-DMAP. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Highly effective synthetic methods for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement: Short syntheses of stemofuran A and eupomatenoid 6

Matrix presented. A new and efficient synthesis of 2-arylbenzofurans has been achieved via a route involving acylation and subsequent [3,3]-sigmatropic rearrangement of oxime ethers. Its synthetic utility is demonstrated by a short synthesis of stemofuran